Water → 2-(Benzyloxy)-5-bromo-1,3-dimethylbenzene

HRID 643607Notes

Reaction equation

HRID 643607 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[C:10]([CH3:15])[C:9]=1[OH:16].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C=O)C>[CH2:17]([O:16][C:9]1[C:8]([CH3:7])=[CH:13][C:12]([Br:14])=[CH:11][C:10]=1[CH3:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 169194-Bromo-2,6-dimethylphenol

Product 1

HCID 229631332-(Benzyloxy)-5-bromo-1,3-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

39.9 g (286 mmol) K2CO3 were added to a solution of 50.0 g (249 mmol) 2,6-dimethyl-4-bromophenol in 500 mL DMF and stirred for 20 min. Then 34.0 mL (286 mmol) benzylchloride were slowly added dropwise and the reaction mixture was stirred for 3 h at 100° C. bath temperature. After the reaction had ended the mixture was poured onto 500 mL water and exhaustively extracted with EtOAc. The organic phases were combined, dried over Na2SO4 and evaporated down i. vac.

Workup

  1. stirringthe reaction mixture was stirred for 3 h at 100° C. bath temperature
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customevaporated down i

Sources & evidence

ORD record
ord-49a8f8fe66444aec9c4280ef7fa5eb77
Source dataset
uspto-grants-2010_04
Patent number
US07700598B2

Reaction notes

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